And now I’m returning to Shakespeare again, because it’s always a good time to talk about Shakespeare — especially when it’s a Friday and you think to yourself, “What the f*ck am I going to write for today’s Labyrinthian?” That’s more of a ‘Freedman problem’ than a ‘you problem,’ but right now it’s impacting both of us.

The History/Tragedy of Richard III

Richard Gloucester (later Richard III) was Shakespeare’s first great character, and the play Richard III was the work that gave Shakespeare a name in the London scene, even if the play lacked the greatness of his later texts.

Framed in the terms of daily fantasy sports, Richard III was Shakespeare’s first big guaranteed prize pool win. Before writing the play, he was something of an outsider among the cohort of London playwrights. He was just that random guy who had moved to the city from the country and had written plays that were juvenile, grotesquely brutal, and/or sycophantic:

• The Two Gentlemen of Verona: A little Dude, Where’s My Car?-ish
• Titus Andronicus: The early modern equivalent of a torture horror flick
• The three Henry VI plays: The War of the Roses, the story about how the Tudors came to power, written for Elizabeth I, the last Tudor monarch

Before he wrote Richard III, Shakespeare was a little bit like early-career Steph Curry: He had flashes of brilliance, but nothing indicated that he was destined for greatness.

And then, almost as if out of nowhere, Shakespeare wrote Richard III — and he had won the Millionaire Maker.

Who Was Richard III?

The historical person who was Richard III probably wasn’t any worse than the average power-hungry male with money, an army, a family name, and a young nephew king in the 1480s. Historians now suggest that, for a guy who had an almost nonexistent right to the throne, he was probably a decent ruler for the two years he was king.

In Shakespeare’s day, however, Richard III was vilified. The Tudor dynasty existed because Elizabeth’s grandfather, Henry of Richmond (later Henry VII), defeated Richard III at the Battle of Bosworth, and to legitimize their claim to the throne the Tudors discredited Richard. Their historians described him as monstrously shaped and (thus) evil. It’s not a stretch to say that the Tudor propaganda made Richard III out to be the Renaissance equivalent of Adolf Hitler.

And Shakespeare decided to write a play about the rise and fall of this guy — and he managed to do it well.

Richard III the character is a study in contrarianism. Imagine now if someone made a film about Hitler. What would it be like if the film made you like him even though you know he’s evil? Made you aroused by him even though he’s grotesque? Made you hate him once he came to power even though you had cheered for him as he plotted, connived, and dissembled his way to the highest position in the country?

That would be an incredibly hard and maybe even dangerous undertaking.

What this imaginary film does for Hitler is basically what Shakespeare did for Richard III.

If you ever want to see a Shakespeare filmic adaptation that isn’t awful, watch Richard III with Ian McKellen (yes, Gandalf and Magneto) as Richard. The supporting cast of Annette Bening, Robert Downey Jr., Kristin Scott Thomas, and Professor Minerva McGonagall is quite good.

Anyway, the point is that when Shakespeare wrote this play in 1592 or so, he was writing about a guy who had been dead over 100 years and was universally hated.

And he turned that guy basically into Walter White except with a hunched back instead of cancer.

An Anecdote

In 1602 — 10 years after Richard III was first performed — a guy named John Manningham wrote down in his notebook a story that he’d heard. Manningham was a law student at Middle Temple (an Inn of Court in London), and he seems to have attended plays with some regularity. Here’s the story he wrote down (in my own words, so that it’s readable):

Once, the famous actor Richard Burbage was playing the role of Richard III. A female member of the audience grew infatuated with his portrayal of Richard, and she spoke to him after the show, asking him to meet her later that night for a rendezvous. Naturally, she wanted him to be with her in the character of Richard III.

Shakespeare — the wily devil! — overheard this conversation and decided that he’d have some fun at everyone else’s expense. Shakespeare met with the woman that night, and because it was dark she evidently couldn’t see that he wasn’t Burbage or in the character of Richard.

[Intentional shift from past to present tense: Authorial license]

So Shakespeare is being ‘entertained’ by his host when Burbage arrives at the woman’s house. He has the servant send word to her that Richard III is wishing to enter through her front door, to which Shakespeare responds with this message: “William the Conqueror comes before Richard III.”

That story though wonderful is probably untrue, but there are still a few takeaways.

When having sex with strangers, have the lights on.

Shakespeare’s Richard III has the potential to appeal to the sexualized deviancy in people.

Shakespeare and his representation of Richard III are intertwined. It was Shakespeare the playwright who made Richard such a humorously horrible character and Richard who challenged Shakespeare to become a better surveyor of humanity. It’s probably not a coincidence that, when people decided to circulate a ribald story of Shakespeare in his adopted city while he still lived there, the character they pulled into the story is the one now commonly referred to as “Shakespeare’s Richard III.” Ever since his creation, Richard has been quintessentially Shakespearean. What Shakespeare did in this story is very much something that Richard III would’ve done if he were real.

And there’s this point: Shakespeare, like Richard III, was a risk-taker.

Winning Is not the Same as Ruling

I’m reminded of what Robert Baratheon says to Ned Stark in the first episode of Game of Thrones:

You helped me win the Iron Throne. Now help me keep the damn thing.

What too many people in life seem not to understand is that winning and ruling are not identical. They require different skills and strategies.

In Shakespeare’s play, Richard III is wonderful when he’s killing people so that he can gain power. He’s charismatic. He breaks the fourth wall and jokes with the audience. He makes evil seem fun.

But once he gains power he transforms into a monster — by doing exactly what he had done before. He continues to kill people. He turns on allies. He cares not about the realm he’s supposed to rule but only about exercising his power absolutely.

By embracing chaos, he won control. By continuing to embrace chaos, he lost everything, in the end willing to trade his kingdom for a horse so that he might ride away from a certain death.

That which wins kingdoms rarely keeps them.

Chaos Is a Ladder

Think of Petyr Baelish (Littlefinger) from GoT and his Shakespearan words on chaos:

Chaos isn’t a pit. Chaos is a ladder. Many who try to climb it fail and never get to try again. The fall breaks them. And some are given a chance to climb, but they refuse. They cling to the realm, or the gods, or love. Illusions. Only the ladder is real. The climb is all there is.

That is a man who maybe could win a kingdom. He’s an outright Talebian with his Black Swan-esque perception of randomness and even antifragility.

Littlefinger could perhaps become king — but he would be utterly incapable of being king. The climb is not all there is, because no ladder goes up forever. Once one reaches the top of the ladder, the surest way to fall is to keep trying to climb.

A Quick Talebian Aside

Nassim Nicholas Taleb might be considered the godfather of modern thought on applied randomness. He’s written books about the benefits of leveraging chaos. In 2007-08, he made unholy sums of money as many veteran investors lost half of their holdings.

Taleb clearly understands the difference between winning and ruling, even if he doesn’t express his thoughts with those terms. In several places, Taleb has written about the ‘barbell strategy’ — a method of investment that attempts to be maximally yet reasonably leveraged to volatility but also invested in safety.

As he puts it . . .

Your strategy is to be as hyperconservative and hyperaggressive as you can be instead of being mildly aggressive or conservative.

For Taleb, ruling is about being safe while also opportunistic. In attempting to win a throne, one has little room for safety.

A DFS Application?

This past season on the NFL Daily Fantasy Flex pod Peter Jennings (CSURAM88), Adam Levitan, and I were joined by an outstanding group of guests. Some of them were DFS players who’ve won million-dollar tournaments and established themselves as forces in the industry.

On the Week 8 episode, the guest was Drew Dinkmeyer, who won the 2014 Week 15 Millionaire Maker (and subsequently appeared in a lot of DraftKings commercials). At one point he was talking about the contests he was considering for the slate, and I asked him about how his approach to contest selection and asset allocation has changed since winning the Milly Maker.

Here’s (some of) what he said:

I’ve really cut back on qualifiers. After kind of going through this period after winning the Milly Maker I was firing hard at the qualifiers, and that ends up being a very costly game if you’re not successful. So I’ve cut way back on those. I barely play them at all.

I focus a little bit more of my attention on just a few lineups that I’m putting into those higher-stakes tournaments that are kind of medium size. I’ve focused a little bit more of my attention in GPPs on a few lineups that I’m really trying to accomplish something with.

And I’ve stopped playing the Milly Maker as well. The payout structure with some of the other tournaments around it is a little bit more favorable. So I’ve cut out some of these really top-heavy prize pool tournaments like the Milly Maker and the qualifiers, and I’ve focused more of my attention on sort of flatter payout-structure tournaments.

Drew won the Millionaire Maker! — and then he stopped playing it.

Keeping a large bankroll is different than trying to build a small one into a large one. Strategies, contests, allocations, denominations, motivations, and sometimes even sports — they can (and sometimes should) change.

Robert Baratheon was a horrible king because he didn’t want to rule. He just wanted to keep on eating, drinking, and whoring his way to an early grave. (I’m paraphrasing his words.)

Richard III was a horrible king because he cared more about the idea of the golden crown than the reality of what it means to wear it.

DFS is a battle. If you fight well enough to become a monarch, be sure to rule your kingdom.

The Labyrinthian: 2017.10, 105

This is the 105th installment of The Labyrinthian, a series dedicated to exploring random fields of knowledge in order to give you unordinary theoretical, philosophical, strategic, and/or often rambling guidance on daily fantasy sports. Consult the introductory piece to the series for further explanation. Previous installments of The Labyrinthian can be accessed via my author page.